HCID 137227839, compound → HCID 67358257, compound

HRID 2243343Notes

Reaction equation

HRID 2243343 reaction equation
[H][H].[NH:3]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]=2[N:5]=[C:4]1[C:12]1[C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[N:25]O)[C:16]=2[CH:15]=[CH:14][CH:13]=1>C(O)C.O1CCCC1.[Ni]>[NH:3]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]=2[N:5]=[C:4]1[C:12]1[C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]([NH2:25])[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 137227839HCID 137227839, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67358257HCID 67358257, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure used in Example 6 is followed. In a 25 ml autoclave, dissolve 43 mg of 4-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 4 ml of ethanol and 4 ml of tetrahydrofuran, add a spatula of Raney activated nickel and then subject to a hydrogen pressure of 1 bar and heat the autoclave at 600 for 12 hours. After cooling, the volume of hydrogen absorbed is 12 ml. After filtration of the catalyst, concentration to dryness under reduced pressure and purification by formation of a paste with diisopropyl ether, in this way we obtain 40 mg of 4-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-9H-fluoren-9(R,S)-ylamine, in the form of a beige powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. additionadd a spatula of Raney
  2. temperatureheat the autoclave at 600 for 12 hours
  3. temperatureAfter cooling
  4. customthe volume of hydrogen absorbed
  5. filtrationAfter filtration of the catalyst, concentration to dryness
  6. customunder reduced pressure and purification by formation of a paste with diisopropyl ether

Sources & evidence

ORD record
ord-13428ca3f0464edf97a8816f65cb9c05
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

Loading…